UPDATE: 2/28/13: I have removed old content on this post that no longer worked and replaced it with a solution that works as of today. I will do my best to keep this post updated as technology changes. Thanks for visiting!
UPDATE: 3/30/12: See the warnings about syncing Outlook with your iPhone in this post, but note that those experiences are from almost a year ago, and things have changed.
UPDATE: 7/28/11: This post refers to syncing Outlook for WINDOWS (all versions, as far as I can tell) with your iPhone. I have not yet found a solution for syncing Outlook 2011 for MAC tasks directly with iPhone. I did find this article about syncing to iCal and if that works successfully, you can then sync tasks easily from iCal to iPhone via iCloud. I can not speak to how well it works. These difficulties, to me, are sufficient reason to recommend AGAINST Outlook for Mac as a productivity solution. For other suggestions of productivity tools for Mac users, see this post and this post.
I used Outlook to run my life for almost a decade, and the majority of the training I do is still using Outlook as the support tool. I also show you in my book how to adapt to Outlook my Empowered Productivity System for managing the details of your life and work. I am a fan and think it is a very powerful PIM (personal information manager) that can easily handle the complexity of your life. The one shortcoming is if you need to share calendars or other information, it’s easiest if you are running an Exchange server and this doesn’t make sense for everyone (technically, you can sync your Outlook calendar with Google and share it that way, although I’d hardly say it’s seamless).
A question I get a lot is how to sync Outlook Tasks with an iPhone. The technology has changed since I originally wrote this post more than three years ago, and I will attempt to keep it updated with the latest information. Some of the comments below may deal with prior content that has since been removed. Also, these are instructions for those NOT using a corporate Exchange server. If you are using an Exchange server, your Outlook tasks should be appearing in the Reminders app on your iPhone. If you don’t like how that works, check out IMExchange2 which has worked really well in my experience.
Syncing Outlook Tasks with iPhone is much harder than it should be. However, if you need to do this, I can offer you three suggestions: MilkSync/Remember the Milk, hosted Exchange for individuals, or CompanionLink/DejaOffice.
This first option gets excellent reviews on iTunes and has great customer service. This is the Remember the Milk app for iPhone, together with MilkSync for syncing with Microsoft Office. These provide a two-way sync but only works with the Pro version of RTM, which as of this writing is $25/year. You can try MilkSync free for 15 days without a pro account. This is the option I recommend you try first.
A second option is that hosted Exchange for individuals is now available for a nominal fee, from Office365.com and also from other providers. This means that for a small monthly subscription (usually around $4-$5/month), you will no longer use the “local” version of Outlook that is installed on your PC, but instead have your Outlook hosted “in the Cloud,” which then allows you to select “Microsoft Exchange” when setting up a new account in “Mail, Contacts, Calendars” on iPhone. Your tasks should sync directly into the Reminders app on iPhone, but as I mentioned above, if you don’t like how that works, you can try a third-party app called IMExchange2.
The third option is not well recommended in the app store, but in the interest of being thorough, I thought I would include it: CompanionLink (on your PC) and DejaOffice (on your iPhone). The instructions for this are as follows:
1. Install CompanionLink on your PC.
2. Install the free DejaOffice app on the iPhone.
3. Configure CompanionLink to use DejaCloud as the sync method.
4. Select “Microsoft Outlook” as the database.
5. Click the Sync button.
You can automate the sync on a timer, as often as every 15 minutes.
Please note that I am not affiliated with any of these companies in any way, and this technology seems to be ever-changing. But I will do my best to keep this post updated with information as I get it. If you try any of these options, I would love to hear about your results! You can email me directly at maura(at)regainyourtime(dot)com.
Don’t forget, to learn a great system for managing your tasks, calendar, email, and all the details of your life and work, check out my training for individuals, groups, and companies, and also my book!
I hope you have found this helpful. Good luck!